Carbon Dioxide → HCID 86618376, compound

HRID 2098648Notes

Reaction equation

HRID 2098648 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[CH:10]=[CH:9][S:8][C:6]=2[N:7]=1.[Li]CCCC.[C:22](=[O:24])=[O:23]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[CH:10]=[C:9]([C:22]([OH:24])=[O:23])[S:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 280Carbon Dioxide2×HCID 130381892-Chloro-4-(morpholin-4-yl)thieno(2,3-d)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 86618376HCID 86618376, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2-Chloro-4-morpholinothieno[2,3-d]pyrimidine (500 mg) was cooled to −78° C. in 50 mL of THF before adding 1.3 eq of a 2.5M solution of nBuLi in hexanes. The reaction was stirred at −78° C. for 30 minutes before warming to −40° C. for several minutes to allow for complete formation of the lithium anion. The reaction was then re-cooled to −78° C. and carbon dioxide gas evolved from dry ice was bubbled in via cannula to the reaction solution for 1 hour. The reaction was then slowly warmed to 0° C. over 30 minutes and the THF was concentrated by rotovap. The reaction was then quenched with water and extracted with Ethyl Acetate to remove any 2-chloro-4-morpholinothieno[2,3-d]pyrimidine. The aqueous layer was then brought to pH of 2-3 by adding concentrated HCl. The resultant solid that crashed out of the aqueous layer was then collected by Buchner funnel, rinsed with water and dried overnight under vacuum to yield 494 mg of 2-chloro-4-morpholinothieno[2,3-d]pyrimidine-6-carboxylic acid.

Workup

  1. temperaturebefore warming to −40° C. for several minutes
  2. temperatureThe reaction was then re-cooled to −78° C.
  3. customwas bubbled in via cannula to the reaction solution for 1 hour
  4. temperatureThe reaction was then slowly warmed to 0° C. over 30 minutes
  5. concentrationthe THF was concentrated by rotovap
  6. customThe reaction was then quenched with water
  7. extractionextracted with Ethyl Acetate
  8. customto remove any 2-chloro-4-morpholinothieno[2,3-d]pyrimidine
  9. additionby adding concentrated HCl
  10. customwas then collected by Buchner funnel
  11. washrinsed with water
  12. customdried overnight under vacuum

Sources & evidence

ORD record
ord-198e4b991ae34d2f91db242030262d0d
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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